Diisopropylethylamine → HCID 67407129, compound

HRID 1949652Notes

Reaction equation

HRID 1949652 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:48][CH:49]([CH:76]([CH3:78])[CH3:77])[C:50]([N:52]1[CH2:56][CH2:55][CH:54]2[N:57]([C:70]3[N:75]=[CH:74][CH:73]=[CH:72][N:71]=3)[CH2:58][CH:59]([C:60]3[C:68]4[C:63](=[CH:64][C:65]([F:69])=[CH:66][CH:67]=4)[NH:62][CH:61]=3)[CH:53]12)=[O:51]>CN1C(=O)CCC1.C(OCC)C>[C:4]([O:3][C:1](=[O:2])[N:8]([CH:9]([C:11](=[O:13])[NH:48][CH:49]([C:50]([N:52]1[CH2:56][CH2:55][CH:54]2[N:57]([C:70]3[N:75]=[CH:74][CH:73]=[CH:72][N:71]=3)[CH2:58][CH:59]([C:60]3[C:68]4[C:63](=[CH:64][C:65]([F:69])=[CH:66][CH:67]=4)[NH:62][CH:61]=3)[CH:53]12)=[O:51])[CH:76]([CH3:77])[CH3:78])[CH3:10])[CH3:14])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67410757HCID 67410757, compound

Product 1

HCID 67407129HCID 67407129, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution containing Boc-N(Me)Ala-OH (75 mg, 0.37 mmol) in anhydrous NMP (3 mL) was cooled to 0° C. HATU (140 mg, 0.37 mmol) and DIPEA (52 mg, 0.42 mmol) were added followed by the addition of 73 (148 mg, 0.35 mmol) in anhydrous NMP (3 mL). The reaction mixture was slowly warmed to ambient temperature. After 4 h, the reaction mixture was diluted with diethyl ether and washed successively with water, aqueous NaHCO3, water and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 202 mg of crude 74 which was used without further purification. Mass spectrum, m/z [608] (M+H)+.

Workup

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. washwashed successively with water, aqueous NaHCO3, water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 202 mg of crude 74 which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-a4e2f3cfdbd14a4fa64d029387ec5aad
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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